Pressure-accelerated copper-free cycloaddition of azide and alkyne groups pre-organized in the crystalline state at room temperature

被引:26
作者
Chen, Hao [1 ]
Ni, Ben-Bo [1 ]
Gao, Fan [1 ]
Ma, Yuguo [1 ]
机构
[1] Peking Univ, Coll Chem, Minist Educ,Key Lab Polymer Chem & Phys, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
PHENYL-PERFLUOROPHENYL STACKING; SOLID-STATE; CLICK CHEMISTRY; PHASE-BEHAVIOR; PI-STACKING; BENZENE; POLYMERIZATION; INHIBITORS; COMPLEXES;
D O I
10.1039/c2gc36069a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have designed a supramolecular system to pre-organize the azide and alkyne functional groups via electrostatic and arene-perfluoroarene interactions. After pre-organization, high pressure was applied to accelerate the copper-free cycloaddition of the azide and alkyne groups in the crystalline state.
引用
收藏
页码:2703 / 2705
页数:3
相关论文
共 65 条
[1]  
Accelrys Software I., 2010, MAT STUD REL NOT REL
[2]   A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].
Agard, NJ ;
Prescher, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047
[3]   Switching stereocontrol in the high pressure-induced hetero-Diels-Alder reaction [J].
Al-Badri, H ;
Collignon, N ;
Maddaluno, J ;
Masson, S .
CHEMICAL COMMUNICATIONS, 2000, (13) :1191-1192
[4]   Binary organogelators which show light and temperature responsiveness [J].
Ayabe, M ;
Kishida, T ;
Fujita, N ;
Sada, K ;
Shinkai, S .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (15) :2744-2747
[5]   Mechanically-Induced Chemical Changes in Polymeric Materials [J].
Caruso, Mary M. ;
Davis, Douglas A. ;
Shen, Qilong ;
Odom, Susan A. ;
Sottos, Nancy R. ;
White, Scott R. ;
Moore, Jeffrey S. .
CHEMICAL REVIEWS, 2009, 109 (11) :5755-5798
[6]   Phenyl-perfluorophenyl stacking interactions: A new strategy for supermolecule construction [J].
Coates, GW ;
Dunn, AR ;
Henling, LM ;
Dougherty, DA ;
Grubbs, RH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :248-251
[7]   Phenyl-perfluorophenyl stacking interactions: Topochemical[2+2] photodimerization and photopolymerization of olefinic compounds [J].
Coates, GW ;
Dunn, AR ;
Henling, LM ;
Ziller, JW ;
Lobkovsky, EB ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3641-3649
[8]   Arene-perfluoroarene interactions in crystal engineering.: Part 3.: Single-crystal structures of 1 : 1 complexes of octafluoronaphthalene with fused-ring polyaromatic hydrocarbons [J].
Collings, JC ;
Roscoe, KP ;
Thomas, RL ;
Batsanov, AS ;
Stimson, LM ;
Howard, JAK ;
Marder, TB .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (11) :1410-1417
[9]  
Feast W. J., 2001, ANGEW CHEM INT EDIT, P505
[10]   Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component List- Barbas-Mannich reaction [J].
Hayashi, Y ;
Tsuboi, W ;
Shoji, M ;
Suzuki, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11208-11209